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6 Things I've Learned About Designing + Selling Merch Since 2017

Not everyone wants to wear a shirt with the f-word on it

Brendan Leonard's avatar
Brendan Leonard
Nov 30, 2025
∙ Paid

[NOTE: This is a post I created for Patreon supporters, so I thought I’d put it here for paid Substack subscribers as well]

You probably got 150+ emails on Black Friday, which is basically a national holiday in the United States at this point. I of course send out an email on Black Friday every year, but it’s because my regular Friday Inspiration email comes out on—wait for it—Fridays. So I compromise a little bit, and VERY RELUCTANTLY put some links to the stuff I sell in my online shop at the very bottom, just in case anyone reading the newsletter would like to buy anything while they’re in the mood to buy things, the holiday season being the most likely time people will buy things, and all that.

I have been selling shirts, hats, coffee mugs, posters, and other products with my designs on them since 2017. I enjoy designing this stuff, but like most creatives, I have a love/hate relationship with selling it. It’s pretty cool to see someone in the wild wearing a t-shirt or a hat you made, and I try to only “market” it with what I’m comfortable with, not trying to push or trick people into buying things they don’t need. I thought it might be fun to share a little behind-the-scenes of how it works for me, and a few things I’ve learned over the past few years:

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